IP Library Granted Patent US 8,664,422
Granted Patent B2
US 8,664,422 · App. 13/933,461 · Granted Mar 4, 2014

Silicone compositions and methods for preparing them

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Quick Facts
Patent No.
US 8,664,422
App. No.
13/933,461
Granted
Mar 4, 2014
Kind
B2
Abstract

A silicone composition comprising a formula: (M 1 ) a (D 1 ) b (D 2 ) c wherein M 1 =R 1 R 2 R 3 SiO 1/2 , D 1 =R 4 R 5 SiO 2/2 ; and D 2 =R 6 R 7 SiO 2/2 ; wherein R 1 is independently at each occurrence a monovalent hydrocarbon radical comprising a reactive end-group other than an amino group; R 6 comprises a monovalent poly(oxyalkyl)hydrocarbon radical; and R 2 , R 3 , R 4 , R 5 , and R 7 are independently monovalent hydrocarbon radicals; wherein a, b, and c are stoichiometric subscripts that are zero or positive subject to the following limitations: a is greater than or equal to 2; c is greater than or equal to 1; and when b=0, a+c is greater than or equal to 3 is disclosed.

Claims (20)

1. A method to form a silicone composition having a formula: (M 1 ) a (D 1 ) b (D 2 ) c , comprising:

reacting a silicone having a formula (M 1 ) a (D 1 ) p with a cyclic hydrosiloxane of formula (D 5 ) q to form an intermediate organosilicone hydride having a formula (M) a (D 1 ) b , (D 3 ) c , wherein M 1 =R 1 R 2 R 3 SiO 1/2 ; D 1 =R 4 R 5 SiO 2/2 ; and D 3 and D 5 are each R 30 HSiO 1/2 ; wherein R 1 is independently at each occurrence a monovalent hydrocarbon radical comprising a reactive end-group other than an amino group; R 2 , R 3 , R 4 , R 5 , and R 30 are independently monovalent hydrocarbon radicals; and wherein a, b, c, p and q are stoichiometric subscripts that are zero or positive subject to the following limitations: q has a value of greater than or equal to 3; a=2; c is greater than or equal to 1; and

reacting the intermediate organosilicone hydride with an unsaturated polyether to form the silicone composition of formula: (M 1 ) a (D 1 ) b (D 2 ) c wherein D 2 =R 6 R 7 SiO 2/2 ; wherein R 6 comprises a monovalent poly(oxyalkyl) hydrocarbon radical; and R 7 is a monovalent hydrocarbon radical; and wherein a, b, and c are stoichiometric subscripts that are zero or positive subject to the following limitations: a has a value of 2; and c is greater than or equal to 1 wherein the reactive end-groups are selected from the group consisting of hydroxyaromatic radicals, hydroxycycloaliphatic radicals, carboxyaromatic radicals, carboxyaliphatic radicals, carboxycycloaliphatic radicals, epoxyaromatic radicals, epoxyaliphatic radicals, and epoxycycloaliphatic radicals.

2. The method of claim 1 , wherein the unsaturated polyether has a formula

wherein R 9 is a divalent hydrocarbon radical having 2 to 20 carbon atoms; R 10 , R 33 , R 34 , and R 35 are each independently a hydrogen atom or a monovalent hydrocarbon radical having 1 to 20 carbon atoms; d has a value from 1 to 100; e is greater than or equal to zero; and W is a divalent hydrocarbon radical having from one to 60 carbon atoms.

3. The method of claim 2 , wherein R 33 is selected from the group consisting of H and CH 3 ; or mixtures thereof.

4. The method of claim 2 , wherein R 33 is CH 3 .

5. The method of claim 4 , wherein the unsaturated polyether is taken in an amount that is greater than or equal to about 20 mole percent excess relative to the amount of the intermediate organosilicone hydride.

6. The method of claim 2 , wherein the cyclic hydrosiloxane is cyclotetramethyltetrahydrosiloxane.

7. The method of claim 1 , wherein the unsaturated polyether has a formula

CH 2 ═C(R 25 )—CH 2 (—OCH 2 CH 2 ) m (—O 2 CH(CH 3 )) n (—OCH 2 CH(C 2 H 5 )) o —OR 26

wherein R 25 is hydrogen or methyl, R 26 is a hydrogen or monovalent hydrocarbon radical, m is 1 to 20; n is or to 20, and o is from zero to 20.

8. The method of claim 7 , wherein R 25 is hydrogen.

9. A silicone composition prepared from the method of claim 1 .

10. A silicone composition prepared from the method of claim 2 .

11. A silicone composition prepared from the method of claim 3 .

12. A silicone composition prepared from the method of claim 4 .

13. A silicone composition prepared from the method of claim 5 .

14. A silicone composition prepared from the method of claim 6 .

15. A silicone composition prepared from the method of claim 7 .

Assignments (19)
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS Recorded Mar 31, 2023
From: BNP PARIBAS
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063259/0133 →
RELEASE OF SECURITY INTEREST Recorded Mar 30, 2023
From: KOOKMIN BANK NEW YORK
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063197/0373 →
RELEASE OF SECURITY INTEREST Recorded Nov 11, 2020
From: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 054336/0023 →
SECOND LIEN TERM LOAN PATENT AGREEMENT Recorded Jun 5, 2019
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: KOOKMIN BANK, NEW YORK BRANCH, AS ADMINISTRATIVE AGENT
Reel/Frame 049388/0220 →
FIRST LIEN TERM LOAN PATENT AGREEMENT Recorded Jun 5, 2019
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: BNP PARIBAS, AS ADMINISTRATIVE AGENT
Reel/Frame 049387/0782 →
ABL PATENT AGREEMENT Recorded Jun 5, 2019
From: MOMENTIVE PERFORMANCE MATERIALS INC.; MOMENTIVE PERFORMANCE MATERIALS GMBH
To: CITIBANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 049388/0252 →
RELEASE OF SECURITY INTEREST Recorded May 15, 2019
From: BOKF, NA
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 049194/0085 →
RELEASE OF SECURITY INTEREST Recorded May 15, 2019
From: BOKF, NA
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 049249/0271 →
BANKRUPTCY ORDER TO RELEASE SECURITY INTEREST AT REEL/FRAME NO. 032736/0457 Recorded Nov 21, 2017
From: BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL AGENT
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 044203/0513 →
BANKRUPTCY ORDER TO RELEASE SECURITY INTEREST AT REEL/FRAME NO. 032736/471 Recorded Aug 20, 2017
From: BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL AGENT
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 043608/0018 →
NOTICE OF CHANGE OF COLLATERAL AGENT - ASSIGNMENT OF SECURITY INTEREST IN INTELLECTUAL PROPERTY Recorded Mar 6, 2015
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A. AS COLLATERAL AGENT
To: BOKF, NA, AS SUCCESSOR COLLATERAL AGENT
Reel/Frame 035136/0457 →
NOTICE OF CHANGE OF COLLATERAL AGENT - ASSIGNMENT OF SECURITY INTEREST IN INTELLECTUAL PROPERTY - SECOND LIEN Recorded Mar 6, 2015
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A. AS COLLATERAL AGENT
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TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENT RIGHTS Recorded Nov 20, 2014
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SECURITY INTEREST Recorded Oct 27, 2014
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To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL AGENT
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SECURITY INTEREST Recorded Oct 27, 2014
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SECURITY INTEREST Recorded Apr 22, 2014
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SECURITY INTEREST Recorded Apr 22, 2014
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL AGENT
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SECURITY INTEREST Recorded Apr 22, 2014
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
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SECURITY INTEREST Recorded Apr 22, 2014
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 032754/0774 →